Tetrahydrofuran → HCID 59750392, compound

HRID 499586Notes

Reaction equation

HRID 499586 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC[Si](C)(C)C)=[O:25])[CH:15]=[CH:14][CH:13]=2)=[N:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>CN(C)C=O>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 22939582HCID 22939582, compound

Product 1

HCID 59750392HCID 59750392, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Trimethylsilyl)ethyl 7-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]heptanoate (0.50 g, 1.1 mmol) was dissolved in N,N-dimethylformamide (4 ml), and 1.0 M tetrabutylammonium fluoride solution in tetrahydrofuran (2.6 ml, 2.6 mmol) was added thereto. The reaction mixture was stirred for 30 minutes and concentrated under reduced pressure. Trifluoroacetic acid (5 ml) was added to the residue, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was subjected to a silica gel (40 g) column chromatography. The fractions eluted with hexane-ethyl acetate (1:1, v/v) were collected and concentrated. The residue was recrystallized from ethanol-hexane to give the titled compound (0.24 g, 61%) as white crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTrifluoroacetic acid (5 ml) was added to the residue
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. washThe fractions eluted with hexane-ethyl acetate (1:1
  5. customv/v) were collected
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-847609f59ecb4c4caafd3844aa7758a4
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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